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Acetone → tert-butyl (6R,7R)-6-(3,4-dichlorophenyl)-7-[(1S)-1,2-dihydroxyethyl]-1,4-oxazepane-4-carboxylate

HRID 1022649
Notes
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Reaction equation

HRID 1022649 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@H](C=C)O[CH2:13][CH2:12][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C[N+]1([O-])CC[O:29]CC1.[CH3:33][C:34]([CH3:36])=[O:35].[OH2:37]>C(#N)C.[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@H:33]([C@@H:34]([OH:35])[CH2:36][OH:29])[O:37][CH2:13][CH2:12][N:11]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 82029Methyl morpholine oxideHCID 66974991tert-butyl (6R,7S)-6-(3,4-dichlorophenyl)-7-ethenyl-1,4-oxazepane-4-carboxylate

Product 1

HCID 66975748tert-butyl (6R,7R)-6-(3,4-dichlorophenyl)-7-[(1S)-1,2-dihydroxyethyl]-1,4-oxazepane-4-carboxylate

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalyst
HCID 6342AcetonitrileSolvent

Procedure

To a mixed solution of tert-butyl (6R,7S)-6-(3,4-dichlorophenyl)-7-ethenyl-1,4-oxazepane-4-carboxylate (1.08 g) and 4-methylmorpholine N-oxide (680 mg) in acetonitrile (6 mL)/acetone (6 mL)/water (6 ml) was added osmium(VIII) oxide immobilized catalyst I (Wako Pure Chemical Industries, Ltd. cat. 153-02581) (700 mg), and the mixture was stirred under nitrogen purging at room temperature overnight. The catalyst was filtered off through celite, and the filtrate was concentrated. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated (product about 1.07 g). 900 mg therefrom was purified by HPLC (column: Sunrise C18-SAC 20×150 mm, mobile phase: water/acetonitrile (containing 5 mM ammonium acetate)) to give the title compound (diastereomer having a shorter retention time) (610 mg) as a colorless oil.

Workup

  1. filtrationThe catalyst was filtered off through celite
  2. concentrationthe filtrate was concentrated
  3. additionWater was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated (product about 1.07 g)
  8. custom900 mg therefrom was purified by HPLC (column: Sunrise C18-SAC 20×150 mm, mobile phase: water/acetonitrile (containing 5 mM ammonium acetate))

Sources & evidence

ORD record
ord-c064bb15e4534bb08e9f555360fd9f4d
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08722662B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes